Conventional methods of producing O-aryl N-(6-alkoxy-2-pyridyl)-N-alkylthiocarbamates such as the O-(5,6,7,8-tetrahydro-2-naphthyl) N-(6-methoxy-2-pyridyl)-N-methylthiocarbamate indicated by the below Formula (4) have included a method of reacting tetrahydro-2-naphthol (1) with thiophosgene to synthesize tetrahydro-2-naphthylchlorothioformate, then inducing a reaction with 6-methoxy-2-methylaminopyridine (3) as indicated by the reaction scheme i), and a method of reacting 6-methoxy-2-methylaminopyridine (3) and thiophosgene to synthesize N-(6-methoxy-2-pyridyl)-N-methylthiocarbamoyl chloride (5), then inducing a reaction with tetrahydro-2-naphthol (1) as indicated by the reaction scheme ii) (see Patent Document 1)

However, these methods involve the use of thiophosgene, a highly toxic compound which must be produced and used under strictly controlled conditions to ensure the safety of workers, and the transport of which is limited. Therefore, industrial procedures using thiophosgene can be considered to be very inconvenient.
For this reason, various methods not using thiophosgene have been proposed. Among these, methods using carbon disulfide are useful for being safe and cheaply performed (see Patent Document 2 and Patent Document 3).
That is, as indicated by the following reaction scheme iii), a reaction is induced between 6-methoxy-2-methylaminopyridine (3) and carbon disulfide to obtain sodium dithiocarbamate (6), which is then reacted with tetrahydronaphthyl-(2,4-dinitrophenyl) ether (7) to obtain the target compound (4). Alternatively, a reaction is induced between sodium dithiocarbamate (6) and 1-chloro-2,4-dinitrobenzene (8) to obtain a dithiocarbamic acid active ester (9), which is then reacted with tetrahydronaphthol (1) to obtain the target compound (4).
Patent Document 1: JP-B S61-30671Patent Document 2: JP-B H6-35442Patent Document 3: P-B H6-74250